3-(Dimethylamino)propyl chloride hydrochloride → Dimaprit hydrochloride

HRID 1704375Notes

Reaction equation

HRID 1704375 reaction equation
[ClH:1].[CH3:2][N:3]([CH3:8])[CH2:4][CH2:5][CH2:6][Cl:7].[NH2:9][C:10]([NH2:12])=[S:11]>C(O)C>[ClH:7].[ClH:1].[CH3:2][N:3]([CH3:8])[CH2:4][CH2:5][CH2:6][S:11][C:10](=[NH:9])[NH2:12]

Participants

4

Reactant 2

HCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 2723790Thiourea

Product 1

HCID 90045Dimaprit hydrochlorideYield 79.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3-(Dimethylamino)-1-chloropropane hydrochloride (79 g) in ethanol (300 ml) was added over a period of 5 mins to a mixture of thiourea (38 g) in ethanol (500 ml). The resultant mixture was boiled under reflux and ethanol (100 ml) was removed by distillation. Further quantities of 3-(dimethylamino)-1-chloropropane hydrochloride (8 g and 4 g) were added after 30 hrs and 54 hrs. refluxing. After the mixture had boiled under reflux for a total of 78 hours the solvent was removed by evaporation to give a moist solid which was filtered off and recrystallised from methanol/isopropanol to give the title product (92.9 g, 79%) m.p. 160.5°-161.5°.

Workup

  1. temperatureunder reflux
  2. customethanol (100 ml) was removed by distillation
  3. additionFurther quantities of 3-(dimethylamino)-1-chloropropane hydrochloride (8 g and 4 g) were added after 30 hrs and 54 hrs
  4. temperaturerefluxing
  5. temperatureunder reflux for a total of 78 hours the solvent
  6. customwas removed by evaporation
  7. customto give a moist solid which
  8. filtrationwas filtered off
  9. customrecrystallised from methanol/isopropanol

Sources & evidence

ORD record
ord-2da6704fc9ff4fcc872599f321e83aa4
Source dataset
uspto-grants-1978_11
Patent number
US04126670

Reaction notes

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